Ni-Catalyzed Regioselective 1,2-Dicarbofunctionalization of Olefins by Intercepting Heck Intermediates as Imine-Stabilized Transient Metallacycles

Shrestha, Bijay; Basnet, Prakash; Dhungana, Roshan K.; KC, Shekhar; Thapa, Surendra; Sears, Jeremiah M.; Giri, Ramesh

doi:10.1021/jacs.7b06340

Title: Ni-Catalyzed Regioselective 1,2-Dicarbofunctionalization of Olefins by Intercepting Heck Intermediates as Imine-Stabilized Transient Metallacycles

Journal Article · 23 July 2017 · Journal of the American Chemical Society

DOI: https://doi.org/10.1021/jacs.7b06340 · OSTI ID:1399511

Shrestha, Bijay ^[1]; Basnet, Prakash ^[1]; Dhungana, Roshan K. ^[1]; KC, Shekhar ^[1]; Thapa, Surendra ^[1]; Sears, Jeremiah M. ^[2];

^[1]

Univ. of New Mexico, Albuquerque, NM (United States)
Sandia National Lab. (SNL-NM), Albuquerque, NM (United States)

We disclose a strategy for Ni-catalyzed regioselective dicarbofunctionalization of olefins in styrene derivatives by intercepting Heck C(sp³)-NiX intermediates with arylzinc reagents. This approach utilizes a readily removable imine as a coordinating group that plays a dual role of intercepting oxidative addition species derived from aryl halides and triflates to promote Heck carbometallation, and stabilizing the Heck C(sp³)-NiX intermediates as transient metallacycles to suppress β-hydride elimination and facilitate transmetalation/reductive elimination steps. This method affords diversely-substituted 1,1,2-riarylethyl products that occur as structural motifs in various natural products.

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Research Organization:: Sandia National Laboratories (SNL-NM), Albuquerque, NM (United States)

Sponsoring Organization:: USDOE National Nuclear Security Administration (NNSA)

Grant/Contract Number:: AC04-94AL85000

OSTI ID:: 1399511

Report Number(s):: SAND--2017-7180J; 655131

Journal Information:: Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 31 Vol. 139; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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Nickel-catalyzed carbodifunctionalization of N -vinylamides enables access to γ-amino acids Yang, Zhi-Fang; Xu, Chang; Zheng, Xing Chemical Communications, Vol. 56, Issue 17 https://doi.org/10.1039/c9cc09866f	journal	January 2020
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Intermolecular selective carboacylation of alkenes via nickel-catalyzed reductive radical relay Zhao, Xian; Tu, Hai-Yong; Guo, Lei Nature Communications, Vol. 9, Issue 1 https://doi.org/10.1038/s41467-018-05951-6	journal	August 2018
Pd‐Catalyzed Dearomatization of Indole Derivatives via Intermolecular Heck Reactions ^† Yang, Ping; Xu, Ren‐Qi; Zheng, Chao Chinese Journal of Chemistry, Vol. 38, Issue 3 https://doi.org/10.1002/cjoc.201900509	journal	January 2020
Nickel‐Catalyzed Asymmetric Reductive 1,2‐Carboamination of Unactivated Alkenes He, Jun; Xue, Yuhang; Han, Bo Angewandte Chemie, Vol. 132, Issue 6 https://doi.org/10.1002/ange.201913743	journal	December 2019
Coordination Assisted Distal C−H Alkylation of Fused Heterocycles Ramakrishna, Kankanala; Biswas, Jyoti Prasad; Jana, Sadhan Angewandte Chemie, Vol. 131, Issue 39 https://doi.org/10.1002/ange.201907544	journal	July 2019
Enantioselective Radical Addition/Cross‐Coupling of Organozinc Reagents, Alkyl Iodides, and Alkenyl Boron Reagents Chierchia, Matteo; Xu, Peilin; Lovinger, Gabriel J. Angewandte Chemie International Edition, Vol. 58, Issue 40 https://doi.org/10.1002/anie.201908029	journal	August 2019
Nickel-Catalyzed Asymmetric Reductive Diarylation of Vinylarenes Anthony, David; Lin, Qiao; Baudet, Judith Angewandte Chemie International Edition, Vol. 58, Issue 10 https://doi.org/10.1002/anie.201900228	journal	February 2019
Electrochemical Difunctionalization of Olefines: Access to Selenomethyl‐Substituted Cyclic Ethers or Lactones Meng, Xiu‐Jin; Zhong, Ping‐Fu; Wang, Yu‐Mei Advanced Synthesis & Catalysis, Vol. 362, Issue 3 https://doi.org/10.1002/adsc.201901115	journal	December 2019
Alkylarylation of styrenes via direct C(sp ³ )–Br/C(sp ² )–H functionalization mediated by photoredox and copper cooperative catalysis Yong, Xin; Han, Ya-Fei; Li, Yang Chemical Communications, Vol. 54, Issue 91 https://doi.org/10.1039/c8cc07587e	journal	January 2018
Unified and practical access to ɤ-alkynylated carbonyl derivatives via streamlined assembly at room temperature Lv, Xu-Lu; Shu, Wei Communications Chemistry, Vol. 2, Issue 1 https://doi.org/10.1038/s42004-019-0219-z	journal	October 2019
Nickel(0)-catalyzed linear-selective hydroarylation of unactivated alkenes and styrenes with aryl boronic acids Lv, Honggui; Xiao, Li-Jun; Zhao, Dongbing Chemical Science, Vol. 9, Issue 33 https://doi.org/10.1039/c8sc02101e	journal	January 2018
Directed nickel-catalyzed 1,2-dialkylation of alkenyl carbonyl compounds Derosa, Joseph; van der Puyl, Vincent A.; Tran, Van T. Chemical Science, Vol. 9, Issue 23 https://doi.org/10.1039/c8sc01735b	journal	January 2018
Nickel-catalyzed intermolecular oxidative Heck arylation driven by transfer hydrogenation Lv, Honggui; Kang, Huiying; Zhou, Biying Nature Communications, Vol. 10, Issue 1 https://doi.org/10.1038/s41467-019-12949-1	journal	November 2019
Nickel‐Catalyzed Asymmetric Reductive Diarylation of Vinylarenes Anthony, David; Lin, Qiao; Baudet, Judith Angewandte Chemie, Vol. 131, Issue 10 https://doi.org/10.1002/ange.201900228	journal	January 2019

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